and even if you aren't going to do an inspection, can you walk it with a couple contractors?

The GC is likely at least a couple of more thousand dollars.  

If I had to choose a couple to look into first, it would be House Hacking, Mid-Term Rental, Short-Term Rental, and BRRRR.

That is a safe harbor from the IRS with a couple of caveats. 

@Loren Souers Couple of questions. 

My partner and I have a couple units we manage as well in Washington DC.

You could ask the Contr to use a flexible compound if this happens again, or maybe even now...https://www.dap.com/products-projects/product-categories/pat...Take pictures of every place it occured....it's easy to forget after a couple years....

I work with a lot of househackers and they're typically on the 12 month cycle, rinse and repeat.While the proposition of acquiring an investment property outside of your market in a "landlord friendly" state may sound appealing, i would recommend you stay local for now and househack another couple of properties over the next few years until you've got some more time / experience under your belt.you would need a management company to cover your property that is outside of your market which would not only take 8-10% of your gross it would also leave you a bit vulnerable to a property management company that you A.)know nothing about and B.)you won't have the experience or cashflow or proximity to deal with any headaches that may arise.i would recommend staying local and househacking your way along for now and then maybe hire a local property management company initially to work with your current/local properties to get a taste of what to expect if and when you begin investing outside of your market.

If a tenant buyer does not exercise the option within the three year period of time, then we can do a couple of things.1. let's say they leave early.

It seems like PSI has grown, a couple landscape companies that way either sold or partnered with PSI because these landscape companies no longer do snow removal and refer people to PSI.